Adam Rich and Ben Lerer carry themselves like guys in the know. Like the city is their personal playground. And any 20-something urban guy is wise to take their advice on the finer points of manhood: booze, food, apparel, and entertainment.

Over the last four years, the two buddies who met at the University of Pennsylvania have parlayed an idea and a $250,000 investment from Pilot Group (the Bob Pittman-led venture firm that backed DailyCandy, a similar newsletter product for women, which recently sold for $125 million) into Thrillist, an e-mail newsletter business focusing on the lifestyles of the American "dude." Not dudes in the Fast Times at Ridgemont High sense, though -- the dudes at the core of Thrillist's 1 million-strong subscription base make money and like to spend it. They drink often, eat well, and dress even better. Or at least aspire to. In other words, any advertiser's dream.

The idea came to Lerer and Rich after they moved to New York following college and noticed a dearth of localized nightlife and lifestyle recommendations for guys their age. Magazines like Esquire and GQ, along with their websites, did a good job of reaching this demographic on a national scale, Lerer and Rich thought, but failed terribly when it came to providing for individual cities. "And they're still not," Lerer, the CEO, says in disbelief.

Today, Thrillist's city-specific newsletters go out to subscribers' inboxes in 12 U.S. markets, including New York, Los Angeles, and Miami. The recipe is the same across the board. Newsletters are delivered daily and for free. The tone is one part irreverence, one part frat-guyese. Each newsletter contains one main write-up on a can't-miss of the day -- a restaurant opening some days, maybe a new product launch on others. "Guys in our demographic care about the same general stuff no matter where they are," says Rich, Thrillist's editor-in-chief. "Where to eat, where they can drink, and where they can get a nice article of clothing."

The newsletters also include links to previous finds on Thrillist.com, sending traffic to the company's website. And perhaps most importantly, for the bottom line, advertisements flank all content in the newsletters and on the website, including occasional sponsored newsletters which closely resemble the usual e-mail blasts. Since subscriptions are free, 100 percent of Thrillist's revenue comes from advertising and sponsorships, such as a recent contest with JetBlue, where winners will be flown for free to a "mystery" location -- one of the cities the airline serves.

Lerer is a bit circumspect when it comes to Thrillist's financial success (2009 revenue will be "between $5 million and $10 million, and it's not going to be $5 million," he says with a smirk). But it's clear by even a cursory look at recent advertisers -- Patron, Bloomingdale's, and Heineken, to name a few -- that even the recession and an ad market in tatters hasn't been enough to slow Thrillist's momentum.

"In the worst ad recession in the universe," Lerer says, "I think it says something that we are thriving."

Still, the founders are far from content. "Right now we're reaching the vast majority of urban guys in the country," Lerer says. "But in the next year or two, we want to be in the top 15 or 20 markets." Thrillist is also set to launch brief restaurant video tours aimed at helping guys familiarize themselves with a restaurant so they can act like they've been there before, and, in turn, impress a date. Slow and steady growth, powered by a vast word-of-mouth network, is the plan.

"When we talk about new ideas, it's not just about whether we can do it, because we can do just about everything we talk about," Rich says. "It's about why are we doing it and does it make sense at the time."